Discover Anna Maria Island with Pineapplefish

Anna Maria Island is a place to fall in love with easily. With it’s rustic charm of an old-Florida, seven miles of coast line and award-winning exquisite sugar-white sandy beaches, average daily temperatures of 26 degrees and 361 days of sunshine a year, it’s not surprising that Anna Maria remains undercommercialized and is renowned as a gem of Florida’s Gulf Coast and is recognized as one of the best beach destinations in the world!

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Browse the collection of Pineapplefish homes

At Pineapplefish, we are proud to have created a selection of rental homes that offer something very special. Either on the Gulf front or the waters edge of our beautiful bays, our locations are exclusive and our homes are beautifully designed, and wonderfully unique. Come take a look at each. Watch our videos, browse our picture galleries and discover which of the Pineapplefish homes is perfect for your Anna Maria Island adventure.

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Where is Anna Maria Island?

The barrier island of Anna Maria is located on the west coast of Central America and is part of Florida’s Gulf Islands. The closest aiport is Sarasota–Bradenton International Airport (SRQ) (20 miles), followed by Tampa International Airport (TPA) (55 miles), and Orlando International Airport (MCO) (130 miles).

Exploring Anna Maria Island

The island is 7 miles long and made up of 3 communities: Bradenton Beach, Holmes Beach and Anna Maria City at the far Northern tip of the island. All of our properties are located within 5 minutes of each other and perfectly placed for all our beautiful beaches and canals, historic piers and other must see spots, aswell as our wonderful boutique stores, and great restaurants and eateries! Take a look at our map, and discover Anna Maria Island.